The Easy Road Again
by Bexish
Summary: Rory could have said no when Jess asked here to bail on his "welcome to Stars Hollow" dinner, but she didn't. Takes place during episode 2x05.


Author's note: Instead of updating one of my other three fics (oops) I wrote this because I watched this episode of Gilmore Girls today and it came to mind. The first bit of dialogue is right from the episode Nick and Norah/Sid and Nancy so I'm not trying to take credit for that! The title is from Real With Me by Cady Groves.

* * *

"So do these open?" Jess gestured toward the window.

Rory shrugged, feeling awkward hovering by her desk. She wasn't always the greatest at meeting new people, and Jess was kind of off-putting. "Yeah, you just have to unlatch them and push," she said. "Why?" Rory could smell Sookie's mac and cheese and was eager to join the rest of the group and have a big plateful, but she didn't necessarily want to leave Jess alone in her bedroom and he didn't seem that interesting in dinner.

"Great," he said. "Shall we?"

"Shall we what?" Rory asked.

"Bail." Jess said it like it should have been obvious, but Rory had never bailed on anything in her life. She had once convinced her mom she didn't have strep throat just so she wouldn't miss a spelling test at school. She could barely talk and was near delirious with a fever, but she had gotten a 99% on that test before she missed the next week of school.

Rory shook her head. "No."

"Why not?"

She scoffed. "It's a Tuesday night in Stars Hollow. There's nowhere to bail to. The 24-hour minimart just closed twenty minutes ago."

That didn't seem to deter Jess. "So we'll just walk around, then. Or sit on a bench and stare at our shoes."

Rory glanced down instinctively. She really had no interest in staring at her ratty gray Converse. "Look, Sookie just made a ton of really great food, and I'm starving and though it may not seem like it right at this moment, it's gonna be fun. Trust me."

"I don't even know you," Jess pointed out.

"Well, don't I look trustworthy?"

"Maybe," Jess said. "Do I?"

Rory looked him over. With the leather jacket, overly gelled hair and the slight smirk he had on his face, she didn't think he looked trustworthy at all. "Maybe," she echoed.

"At least we agree," Jess said, pushing open her bedroom window. He swung one leg out, hovering in the frame for a second. "Well, are you coming or not?"

Even if she said no, it was obvious that Jess wasn't hanging around. If Rory went out in the living room and told everybody that Jess had climbed out her window and disappeared, the party was going to be ruined. Luke would immediately leave to look for him, Sookie would bemoan all the time she had spent cooking and Lorelai would probably rant for a while about how ungrateful and irresponsible Jess was to leave a party that was being held for him. Glancing out her bedroom door, she noticed all the food was still on the kitchen table. "Give me a second," she said, an idea forming. Before she could change her mind she walked out and into the living room.

"Hey Mom, Jess and I are going to eat outside," Rory said. Lorelai nodded absently, already deep into a conversation with Sookie.

"Make sure you shut the back door so bugs don't get in," she said, not even looking up. She didn't seem too concerned about the guest of honor not even wanting to be in the house. Rory glanced at Luke before she walked back out, and he gave her a thumbs up. Rory returned the gesture, a little thrilled that everyone had believed her so easily. She wouldn't consider herself a liar, but she wasn't too bad at it.

Back in her room Jess was still sitting in the windowsill, kicking his heels against the wall. "Lying to mommy?"

"I just didn't want her to worry if I didn't follow her out there."

"How sweet," Jess said sardonically, hopping out the window. "She's got you on a nice little leash there, huh?"

Rory scowled, climbing out the window after him. "No. Don't make me regret following you out here."

"I won't," Jess said, looking around. "So where do we go from here?"

Rory pointed around the backside of their garage. "Go that way. I don't want them to see us if we walk near the living room."

"Well, aren't we paranoid," Jess said, though he followed her directions. "Do you really think they care that we're not in there?"

Jess hadn't been there for the party preparation, so he couldn't possibly know that Sookie had made four main courses just to make sure there would be something Jess liked. Lorelai had even gone out and picked up some Sprite in case Jess didn't like Coke, and Rory knew she hated Sprite. They had just wanted Jess to feel welcome in Stars Hollow and he had bailed at the first opportunity he saw. And so had she. "Yes, I think they would," Rory said, feeling a little guilty. Still, she was a little excited. Ever since she got into Chilton she felt like all she ever did was work. Even her summer had spent taking classes and trying to squeeze in volunteer work, much to Dean's dismay. It was nice to finally just take a little while and hang out with someone new. It wasn't like she was making any friends at Chilton. "You know, Sookie's going to send you and Luke home with a ton of leftovers. You better eat all of them."

"Yes, ma'am."

For a couple of minutes they walked in silence, heading toward the center of town. As Rory had predicted there weren't a lot of people around. Luke's was looking a little sad with all the lights off since he had closed early for the night. Nearly everything around Luke's was already closed, too. It wasn't particularly late but Stars Hollow pretty much shut down after the sun set. Rory thought about going and sitting in the gazebo, but decided against it since Doose's was still open. She wasn't sure if Dean was working tonight but she didn't want him to see her with Jess if he was. Not that there was anything wrong with her hanging out with Jess, but Dean had been kind of irritated lately that she didn't have as much time to hang out with him as usual.

"You took me pretty seriously when I said we could just walk around, huh?" Jess asked as they rounded the corner at Luke's. "I didn't actually mean we just had to walk around forever."

"It's been fifteen minutes," Rory said. "And for the record, I actually had a destination in mind. You're new here. You don't even know where we're going." It wasn't long before Jess found out though. Despite the fact that Rory logically knew that Jess could murder her and dump her body in the lake, Rory had lead him to the little just past Luke's. Even though the town was constantly trying to raise money to repair it and make it a grand spectacle, it didn't even have guard rails. It was little and maybe not entirely safe, but Rory had always liked it there. At nine on a Tuesday night nobody would bother them there.

Jess nearly crashed into her when she stopped abruptly on the middle of the bridge. "This is it?" he asked. When Rory nodded he promptly sat down, his legs dangling over the side. "Cool place. I was starting to think places like that didn't exist in Stars Hollow."

"Hey, we might not be New York but we're plenty cool," Rory argued, sitting down beside him. When she had first met Dean she felt awkward and stupid around him all the time, but sitting here with Jess felt comfortable. Maybe she would actually have a new friend. "I'm sure your hangout in New York was way cooler, though."

Jess snorted. "My hangout? I didn't have a hangout. No one has hangouts anymore. I went to Washington Square Park a lot, though. It's a pretty cool place. There are a lot less preppy stoners than Central Park, anyway."

"That's where David Lee Roth got busted, right?" Rory asked. Rory's dad loved Van Halen and her mom always teased him about how they weren't even cool enough to score cheap weed.

"I'm surprised you know that," Jess said. "I can't picture you as a Van Halen fan."

"I'm not," she admitted. "But I've heard my mom mention them a time or two. I'm more of an N'Sync kind of girl."

Jess studied her for a moment, then shrugged. "I can't tell if you're kidding or not. I could believe it, but it also seems like you're messing with me."

"I can't believe you would think that I would actually listen to N'Sync," Rory said, feigning hurt. "It's like you don't know me at all."

"I don't know you," Jess pointed out. "I know you like to read and you're scared of disappointing your mom and you don't like Van Halen or N'Sync, but that's about it."

"Wait a second, I am not scared of disappointing my mom," she argued.

"Uh huh. So that's why you had to check with her before you snuck out, right?"

"I didn't check with her! I just don't sneak out much."

Jess snorted. "Please, I watched you climb out that window. You've never snuck out in your life, have you?"

Rory picked up a rock and tossed it in the lake, watching the ripples expand. The water looked glassy in the moonlight. "So what if I haven't? I bet you do it all the time, right? Mr. Cool Guy."

"It's not sneaking out if no one cares if you leave."

"I'm sure Luke would care if he found out you left," Rory said.

Jess shrugged. "I doubt it. He's probably annoyed that I'm here at all. He's acting like he's not, but it's totally fake. He's trying too hard to act like he's cool with it."

"He's not annoyed," Rory said. "And he would care if he knew that you left. I've known Luke for a long time. He's a really good guy. He might not act like it, but he does care about people a lot. He wouldn't have offered to let you move in if he didn't really want you too." Rory really wanted to know why exactly Jess was here, but she couldn't bring herself to ask. It wasn't any of her business and truthfully, she was a little scared of what the answer might be. Jess was about as different as possible from anyone she knew. Dean worked in a grocery store and played on a softball league and helped his little sister with her homework, and Jess snuck out and hung out in parks in New York City and got sent to live with a relative he barely knew.

Jess shrugged again. Rory was already noticing that he did that a lot. "Whatever. I'll be eighteen in less than a year anyway and then I can get out of here."

"What about school?" Rory asked. Lorelai had mentioned that Jess was a junior too, so even though he would be eighteen soon he still had two years of school left.

"What about it?" Jess said. Rory winced. Her whole life had been about school and she was more excited about going to Harvard than she had been about anything else. She couldn't imagine having such a cavalier attitude about it. "Oh, don't look at me like that," Jess said, noticing her flinch. "School isn't everything. You can learn without being trapped in some building."

That made Rory feel a little bit better. "It's pretty important though. Don't you want to graduate and go to college? You can do anything you want in college."

"I can do anything I want when I'm eighteen," Jess countered. "I don't need to waste thousands of dollars a year at some other school. Maybe I'll just travel, instead."

"My mom and I are going backpacking in Europe after I graduate," Rory said. "We're going to spend the whole summer just seeing everything we can. We've been planning it for years."

"Well there you go," Jess said. "Maybe I'll do that."

"You would go backpacking alone?" Rory couldn't imagine going on vacation by herself. It would be incredibly lonely.

"Hey, I'm used to doing things by myself," Jess said. "It's no big deal. What's the worst that could happen?"

"You could get murdered," she pointed out. "You could get mugged and you could get murdered and pushed into a canal in Venice."

"So I won't go to Venice then," Jess said. "Little boats aren't for me, anyway. And I could get murdered and pushed into this lake right now, but I'm here anyway."

Rory frowned at him. "Why are you assuming that I would murder you? Maybe you would murder me. You could pull a knife on me at any second."

Jess patted his pockets. "No knives," he said. "Do I really look like the kind of guy who would carry a knife around?"

When she had seen him for the first time earlier Rory might have said yes. When he sort of introduced himself Jess had seemed like he was made entirely of hard edges. But now Rory wasn't sure what kind of guy Jess really was. He seemed like he could be any kind of guy. "Maybe," she said. "I honestly can't tell."

He turned and looked her in the eye, which Rory found to be a little unsettling. No one had ever looked at her in such an appraising way before. Rory counted to six before she blinked and looked away. It wasn't until she did that Jess spoke up. "I can't tell about you, either."

"Oh, please. You probably thought you had me pegged the minute you saw me."

"I thought I did," Jess said. "I know you don't sneak out without telling your mom and you care about other people's feelings. I'm guessing you probably study hard and get good grades, because you look like the type of person who gets good grades. Judging by the uniform sitting on your dresser I'm also guessing you go to some fancy private school, which means you'll probably go to a fancy college too. You read a lot of books, but none of them are stupid teen books with pink covers so you're probably interested in a challenge. You were working on something when I walked into your room and you were typing really quickly, so I'm guessing you're a good writer or you're really anal about planning things out before you start them. Probably both. Because of all that, I'm guessing you have a boyfriend, probably someone who plays football or something at that fancy school of yours." He paused and looked at her. "But I don't know if any of that's true. I can guess all I want, but I'm willing to concede that I don't know the kind of person you are at all."

Rory was uncomfortable with how much of that had been right. He had said just a few minutes ago that he didn't know her, but his guess had pretty much been dead on. Was she really that predictable? She didn't want to be. She was comfortable with who she was, but she didn't necessarily want everyone else to know who she was just by looking at her. "My boyfriend doesn't go to my school," she said lamely. "And he doesn't play football. Just softball."

Jess nodded. "But you do have a boyfriend."

"Yeah, his name is Dean," she said. Jess didn't really seem interested in the fact that he had been right about everything else. He didn't say anything, just stood up and offered her his hand.

"We should get back, right?" Rory nodded, taking his hand. He held on just a second longer than necessary, his thumb brushing the back of her hand as she let go. "You wouldn't want to get in trouble. It would probably be the first time, right?"

"Oh, I've been in trouble before," Rory said, thinking of the dance last year where she had accidentally stayed out with Dean all night. It had blown over pretty quickly, but she had never seen her mom so mad at her before. "See? You don't know everything about me."

"No, I guess I don't," Jess said. He was quiet the whole way back to the house, mostly staring straight ahead or down at his shoes the whole time. Rory wondered if she had said the wrong thing, but they hadn't even really talked that much. She wasn't sure what she could have said to irritate him. If anything, she was the one who should have been allowed to be irritated. She had barely told Jess anything about her life and yet he had practically guessed everything. He was the new mysterious guy, and she was still plain old predictable Rory. She wasn't out to shock people, but she wanted to be the kind of person people actually wanted to get to know. She wanted to know more about Jess, but had figured her out right away. He had no reason to try to get to know her more. He had just met her an hour ago and he already knew all he needed to know.

Back at her house nothing had changed from when they left. As she walked up the back porch she could hear her mom and Sookie laughing in the living room. If anyone had gone back in the kitchen for more food they obviously hadn't looked outside to check on her and Jess. And why would they? Lorelai trusted Rory completely, and aside from the whole dance mix-up she had never given her mom a reason not to.

"Are you coming back inside?" Rory asked, her hand on the doorknob. She could smell the food even from the porch and she was looking forward to finally eating dinner. Her stomach growled at the thought of food. "You must be starving."

"Nah, I'm good," Jess said. "I think I'm going to stay out here for a while. It seems loud in there, you know?"

"Sure," Rory said, even though hanging out with everyone sounded nice to her. "Do you want me to tell Luke you're still out here?"

"He'll figure it out," Jess said, leaning against the railing. "Really, don't worry about it. Go have fun."

Rory nodded and headed back in the house. But even after she settled down in the living room with her food, she was still thinking of Jess sitting out on the back porch. She thought about checking on him when she went out to get a drink, but she decided against it. He had obviously had enough socializing for the day already. No one in the living room seemed particularly bothered that Jess wasn't there with him. Even though they had planned all this for him, they had obviously accepted that he didn't want to be a part of it. For some reason that made Rory kind of sad, and she didn't really know why. It felt a little bit like they had already given up.

It was nearing eleven when everyone got ready to go home. Rory had offered to help Sookie pack up her dishes, but she had waved her off. Another night Rory might have insisted, but she was happy to go in her room and just reflect on the night. She was still kind of in a funk that Jess had figured her out so easily, even if he had said he didn't. The fact that she was even annoyed at all irritated her further, because up until tonight she had felt great with how things were going for her. She did everything she was supposed to do, and it had been working out great for her. She had good grades, a great relationship with her mom and an attractive boyfriend that treated her like a princess. Until then, it had been everything she wanted. Now she wasn't exactly sure what she wanted. She was still happy with everything she had, but she wanted something more.

Pulling back her blankets to get in bed, she noticed a piece of paper sticking out from under her pillow. The handwriting was unfamiliar, but she knew who it was from even before she looked for a signature. Who else would have climbed back in her open bedroom window to leave her a note?

_Don't wait until college to be who you want to be_. _Do whatever you want. Keep people guessing._

He hadn't signed the note, but Rory was sure it was from Jess. She slipped the note back under her pillow, wondering when she would see him again. She didn't know what she wanted to do, but maybe Jess would help her figure it out.


End file.
